# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2263048'
loop_
_audit_author_name
_audit_author_address
'Juanjuan Wang'
;Northwest University
China
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        29
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 Br N O3'
_chemical_formula_sum            'C17 H10 Br N O3'
_chemical_formula_weight         356.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.4496(2)
_cell_length_b                   20.6183(6)
_cell_length_c                   13.2918(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.8540(10)
_cell_angle_gamma                90
_cell_volume                     1471.45(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      57.05

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.584
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14842
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.478
_diffrn_reflns_theta_max         57.048
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2964
_reflns_number_gt                2703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.6028P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.16353(4) 0.57505(2) 0.89669(2) 0.05094(13) Uani 1 1 d . . . . .
O1 O 0.2714(3) 0.38025(10) 0.39124(15) 0.0650(5) Uani 1 1 d . . . . .
O2 O 0.3940(3) 0.33088(8) 0.62531(14) 0.0548(4) Uani 1 1 d . . . . .
O3 O 0.6064(3) 0.41876(7) 0.58761(13) 0.0457(4) Uani 1 1 d . . . . .
N1 N 0.7880(3) 0.28620(8) 0.50633(12) 0.0345(4) Uani 1 1 d . . . . .
C1 C 0.9081(3) 0.24851(9) 0.44270(15) 0.0320(4) Uani 1 1 d . . . . .
C2 C 1.0960(4) 0.20901(11) 0.49647(17) 0.0422(5) Uani 1 1 d . . . . .
H2 H 1.126647 0.210293 0.568224 0.051 Uiso 1 1 calc R U . . .
C3 C 1.2364(4) 0.16850(12) 0.4468(2) 0.0522(6) Uani 1 1 d . . . . .
H3 H 1.359314 0.141984 0.484490 0.063 Uiso 1 1 calc R U . . .
C4 C 1.1961(5) 0.16690(12) 0.3409(2) 0.0508(6) Uani 1 1 d . . . . .
H4 H 1.292008 0.139426 0.306565 0.061 Uiso 1 1 calc R U . . .
C5 C 1.0153(4) 0.20566(11) 0.28639(17) 0.0438(5) Uani 1 1 d . . . . .
H5 H 0.991271 0.204462 0.214679 0.053 Uiso 1 1 calc R U . . .
C6 C 0.8654(4) 0.24695(9) 0.33400(15) 0.0342(4) Uani 1 1 d . . . . .
C7 C 0.6819(4) 0.28453(10) 0.26686(15) 0.0405(5) Uani 1 1 d . . . . .
H7 H 0.685438 0.278608 0.197005 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5080(4) 0.32617(11) 0.28641(17) 0.0429(5) Uani 1 1 d . . . . .
H8 H 0.409368 0.345019 0.228913 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4516(4) 0.34608(10) 0.38416(17) 0.0402(5) Uani 1 1 d . . . . .
C10 C 0.6094(3) 0.32600(9) 0.48252(15) 0.0340(4) Uani 1 1 d . . . . .
C11 C 0.5201(4) 0.35721(10) 0.57304(16) 0.0378(4) Uani 1 1 d . . . . .
C12 C 0.5033(4) 0.45457(10) 0.66095(17) 0.0388(4) Uani 1 1 d . . . . .
C13 C 0.2836(4) 0.48669(11) 0.62977(17) 0.0453(5) Uani 1 1 d . . . . .
H13 H 0.203042 0.484152 0.561448 0.054 Uiso 1 1 calc R U . . .
C14 C 0.1808(4) 0.52312(11) 0.70026(17) 0.0441(5) Uani 1 1 d . . . . .
H14 H 0.029680 0.545379 0.680637 0.053 Uiso 1 1 calc R U . . .
C15 C 0.3059(4) 0.52583(10) 0.79968(16) 0.0371(4) Uani 1 1 d . . . . .
C16 C 0.5293(4) 0.49432(11) 0.83055(17) 0.0429(5) Uani 1 1 d . . . . .
H16 H 0.612196 0.497538 0.898460 0.051 Uiso 1 1 calc R U . . .
C17 C 0.6298(4) 0.45784(11) 0.76008(18) 0.0433(5) Uani 1 1 d . . . . .
H17 H 0.781426 0.435733 0.779402 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.907(2) . ?
O1 C9 1.225(3) . ?
O2 C11 1.189(3) . ?
O3 C11 1.356(3) . ?
O3 C12 1.414(2) . ?
N1 C10 1.271(3) . ?
N1 C1 1.392(3) . ?
C1 C2 1.404(3) . ?
C1 C6 1.424(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.446(3) . ?
C7 C8 1.336(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.445(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.495(3) . ?
C10 C11 1.516(3) . ?
C12 C13 1.369(3) . ?
C12 C17 1.380(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.379(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C12 114.72(16) . . ?
C10 N1 C1 128.96(17) . . ?
N1 C1 C2 113.10(17) . . ?
N1 C1 C6 128.11(17) . . ?
C2 C1 C6 118.79(18) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.69(19) . . ?
C5 C6 C7 116.19(19) . . ?
C1 C6 C7 126.12(19) . . ?
C8 C7 C6 131.5(2) . . ?
C8 C7 H7 114.2 . . ?
C6 C7 H7 114.2 . . ?
C7 C8 C9 128.6(2) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
O1 C9 C8 122.0(2) . . ?
O1 C9 C10 116.2(2) . . ?
C8 C9 C10 121.88(18) . . ?
N1 C10 C9 134.28(19) . . ?
N1 C10 C11 114.36(17) . . ?
C9 C10 C11 111.18(17) . . ?
O2 C11 O3 124.42(19) . . ?
O2 C11 C10 124.47(19) . . ?
O3 C11 C10 111.10(17) . . ?
C13 C12 C17 122.3(2) . . ?
C13 C12 O3 118.3(2) . . ?
C17 C12 O3 119.41(19) . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 Br1 119.35(16) . . ?
C14 C15 Br1 118.52(16) . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C12 C17 C16 118.76(19) . . ?
C12 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C1 C2 -178.9(2) . . . . ?
C10 N1 C1 C6 2.4(3) . . . . ?
N1 C1 C2 C3 -179.7(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
N1 C1 C6 C5 178.54(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C7 -0.9(3) . . . . ?
C2 C1 C6 C7 -179.56(19) . . . . ?
C5 C6 C7 C8 177.8(2) . . . . ?
C1 C6 C7 C8 -2.7(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 O1 -173.1(2) . . . . ?
C7 C8 C9 C10 6.7(4) . . . . ?
C1 N1 C10 C9 3.7(4) . . . . ?
C1 N1 C10 C11 178.27(17) . . . . ?
O1 C9 C10 N1 170.6(2) . . . . ?
C8 C9 C10 N1 -9.3(4) . . . . ?
O1 C9 C10 C11 -4.1(3) . . . . ?
C8 C9 C10 C11 176.01(18) . . . . ?
C12 O3 C11 O2 -9.7(3) . . . . ?
C12 O3 C11 C10 171.30(17) . . . . ?
N1 C10 C11 O2 -76.2(3) . . . . ?
C9 C10 C11 O2 99.7(3) . . . . ?
N1 C10 C11 O3 102.8(2) . . . . ?
C9 C10 C11 O3 -81.4(2) . . . . ?
C11 O3 C12 C13 -86.2(2) . . . . ?
C11 O3 C12 C17 95.9(2) . . . . ?
C17 C12 C13 C14 -1.1(3) . . . . ?
O3 C12 C13 C14 -178.94(19) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C13 C14 C15 Br1 -179.38(17) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
Br1 C15 C16 C17 179.03(16) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
O3 C12 C17 C16 178.56(18) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.062



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2263052'
loop_
_audit_author_name
_audit_author_address
'juanjuan wang'
;Northwest University
China
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        399
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N O3'
_chemical_formula_sum            'C21 H15 N O3'
_chemical_formula_weight         329.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7620(5)
_cell_length_b                   12.9308(9)
_cell_length_c                   15.9453(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.829(2)
_cell_angle_gamma                90
_cell_volume                     1594.73(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2171
_cell_measurement_theta_min      52.70
_cell_measurement_theta_max      3.83

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.476
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15353
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_av_R_equivalents  0.1532
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.834
_diffrn_reflns_theta_max         57.132
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3266
_reflns_number_gt                1822
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3266
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9439(2) 0.74478(11) 0.50655(9) 0.0392(4) Uani 1 1 d . . . . .
O2 O 0.8269(2) 0.67772(12) 0.32866(9) 0.0432(4) Uani 1 1 d . . . . .
O3 O 0.87014(19) 0.50575(11) 0.33740(9) 0.0338(4) Uani 1 1 d . . . . .
N1 N 0.7385(2) 0.50866(12) 0.48782(10) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.5547(3) 0.48264(18) 0.87435(14) 0.0392(6) Uani 1 1 d . . . . .
H1 H 0.542599 0.463652 0.931107 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5282(3) 0.58536(17) 0.84858(14) 0.0368(6) Uani 1 1 d . . . . .
H2 H 0.500972 0.636248 0.888343 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5415(3) 0.61300(16) 0.76633(13) 0.0301(5) Uani 1 1 d . . . . .
H3 H 0.520509 0.682759 0.749772 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5857(3) 0.53991(15) 0.70542(12) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.6133(3) 0.56801(15) 0.61965(12) 0.0235(5) Uani 1 1 d . . . . .
C6 C 0.5502(3) 0.66957(15) 0.58675(12) 0.0248(5) Uani 1 1 d . . . . .
C7 C 0.3888(3) 0.70709(16) 0.60556(13) 0.0298(5) Uani 1 1 d . . . . .
H7 H 0.318632 0.665840 0.638346 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3292(3) 0.80281(16) 0.57752(14) 0.0345(6) Uani 1 1 d . . . . .
H8 H 0.218826 0.826366 0.590872 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4298(3) 0.86451(17) 0.53003(14) 0.0387(6) Uani 1 1 d . . . . .
H9 H 0.389232 0.930720 0.511655 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5887(3) 0.82982(16) 0.50946(14) 0.0348(6) Uani 1 1 d . . . . .
H10 H 0.657581 0.872227 0.476944 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6489(3) 0.73210(15) 0.53639(13) 0.0262(5) Uani 1 1 d . . . . .
C12 C 0.8097(3) 0.69543(16) 0.50409(12) 0.0285(5) Uani 1 1 d . . . . .
C13 C 0.7918(3) 0.59382(16) 0.45821(13) 0.0253(5) Uani 1 1 d . . . . .
C14 C 0.6908(2) 0.49507(15) 0.57038(12) 0.0232(5) Uani 1 1 d . . . . .
C15 C 0.7188(3) 0.39209(15) 0.59943(13) 0.0292(5) Uani 1 1 d . . . . .
H15 H 0.765339 0.342568 0.563543 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6807(3) 0.36337(16) 0.67702(13) 0.0314(5) Uani 1 1 d . . . . .
H16 H 0.695084 0.293273 0.694027 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6193(3) 0.43670(16) 0.73344(13) 0.0276(5) Uani 1 1 d . . . . .
C18 C 0.5977(3) 0.41002(17) 0.81788(14) 0.0357(6) Uani 1 1 d . . . . .
H18 H 0.613494 0.340244 0.835536 0.043 Uiso 1 1 calc R U . . .
C19 C 0.8319(3) 0.59783(17) 0.36782(13) 0.0299(5) Uani 1 1 d . . . . .
C20 C 0.9077(3) 0.50398(18) 0.24930(13) 0.0391(6) Uani 1 1 d . . . . .
H20A H 1.000713 0.553902 0.239628 0.047 Uiso 1 1 calc R U . . .
H20B H 0.803365 0.522779 0.212471 0.047 Uiso 1 1 calc R U . . .
C21 C 0.9639(3) 0.39628(19) 0.23053(15) 0.0487(7) Uani 1 1 d . . . . .
H21A H 1.007626 0.394434 0.174661 0.073 Uiso 1 1 calc R U . . .
H21B H 0.865181 0.349174 0.231687 0.073 Uiso 1 1 calc R U . . .
H21C H 1.055526 0.374712 0.272943 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.219(2) . ?
O2 C19 1.206(2) . ?
O3 C19 1.329(2) . ?
O3 C20 1.459(2) . ?
N1 C13 1.280(2) . ?
N1 C14 1.408(3) . ?
C1 C18 1.362(3) . ?
C1 C2 1.400(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.418(3) . ?
C3 H3 0.9500 . ?
C4 C17 1.424(3) . ?
C4 C5 1.448(3) . ?
C5 C14 1.396(3) . ?
C5 C6 1.482(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.410(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.468(3) . ?
C12 C13 1.505(3) . ?
C13 C19 1.501(3) . ?
C14 C15 1.421(3) . ?
C15 C16 1.348(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.413(3) . ?
C18 H18 0.9500 . ?
C20 C21 1.497(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O3 C20 115.76(17) . . ?
C13 N1 C14 124.79(17) . . ?
C18 C1 C2 119.9(2) . . ?
C18 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C17 117.27(19) . . ?
C3 C4 C5 122.89(18) . . ?
C17 C4 C5 119.58(18) . . ?
C14 C5 C4 117.83(17) . . ?
C14 C5 C6 123.00(18) . . ?
C4 C5 C6 119.08(18) . . ?
C7 C6 C11 117.54(18) . . ?
C7 C6 C5 120.41(19) . . ?
C11 C6 C5 122.04(19) . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.5(2) . . ?
C10 C11 C12 117.1(2) . . ?
C6 C11 C12 122.22(18) . . ?
O1 C12 C11 124.66(19) . . ?
O1 C12 C13 121.1(2) . . ?
C11 C12 C13 113.96(17) . . ?
N1 C13 C19 118.91(18) . . ?
N1 C13 C12 126.25(19) . . ?
C19 C13 C12 114.74(18) . . ?
C5 C14 N1 126.99(17) . . ?
C5 C14 C15 120.76(19) . . ?
N1 C14 C15 112.12(17) . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.65(19) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.97(19) . . ?
C18 C17 C4 119.6(2) . . ?
C16 C17 C4 119.36(19) . . ?
C1 C18 C17 121.1(2) . . ?
C1 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
O2 C19 O3 125.2(2) . . ?
O2 C19 C13 121.8(2) . . ?
O3 C19 C13 112.98(18) . . ?
O3 C20 C21 107.00(18) . . ?
O3 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 C1 C2 C3 1.5(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C17 -1.2(3) . . . . ?
C2 C3 C4 C5 -175.3(2) . . . . ?
C3 C4 C5 C14 166.86(18) . . . . ?
C17 C4 C5 C14 -7.1(3) . . . . ?
C3 C4 C5 C6 -16.4(3) . . . . ?
C17 C4 C5 C6 169.63(17) . . . . ?
C14 C5 C6 C7 135.4(2) . . . . ?
C4 C5 C6 C7 -41.2(3) . . . . ?
C14 C5 C6 C11 -45.0(3) . . . . ?
C4 C5 C6 C11 138.42(19) . . . . ?
C11 C6 C7 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 178.23(18) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C6 -1.8(3) . . . . ?
C9 C10 C11 C12 173.16(19) . . . . ?
C7 C6 C11 C10 2.5(3) . . . . ?
C5 C6 C11 C10 -177.13(17) . . . . ?
C7 C6 C11 C12 -172.29(17) . . . . ?
C5 C6 C11 C12 8.1(3) . . . . ?
C10 C11 C12 O1 51.3(3) . . . . ?
C6 C11 C12 O1 -133.8(2) . . . . ?
C10 C11 C12 C13 -122.6(2) . . . . ?
C6 C11 C12 C13 52.3(2) . . . . ?
C14 N1 C13 C19 -177.74(18) . . . . ?
C14 N1 C13 C12 -1.6(3) . . . . ?
O1 C12 C13 N1 129.0(2) . . . . ?
C11 C12 C13 N1 -56.9(3) . . . . ?
O1 C12 C13 C19 -54.7(3) . . . . ?
C11 C12 C13 C19 119.4(2) . . . . ?
C4 C5 C14 N1 -175.86(18) . . . . ?
C6 C5 C14 N1 7.5(3) . . . . ?
C4 C5 C14 C15 8.8(3) . . . . ?
C6 C5 C14 C15 -167.85(18) . . . . ?
C13 N1 C14 C5 33.2(3) . . . . ?
C13 N1 C14 C15 -151.09(18) . . . . ?
C5 C14 C15 C16 -3.8(3) . . . . ?
N1 C14 C15 C16 -179.80(19) . . . . ?
C14 C15 C16 C17 -3.2(3) . . . . ?
C15 C16 C17 C18 -172.7(2) . . . . ?
C15 C16 C17 C4 4.7(3) . . . . ?
C3 C4 C17 C18 3.7(3) . . . . ?
C5 C4 C17 C18 178.00(19) . . . . ?
C3 C4 C17 C16 -173.74(19) . . . . ?
C5 C4 C17 C16 0.6(3) . . . . ?
C2 C1 C18 C17 1.1(3) . . . . ?
C16 C17 C18 C1 173.7(2) . . . . ?
C4 C17 C18 C1 -3.7(3) . . . . ?
C20 O3 C19 O2 -0.2(3) . . . . ?
C20 O3 C19 C13 179.04(17) . . . . ?
N1 C13 C19 O2 155.2(2) . . . . ?
C12 C13 C19 O2 -21.4(3) . . . . ?
N1 C13 C19 O3 -24.1(3) . . . . ?
C12 C13 C19 O3 159.34(16) . . . . ?
C19 O3 C20 C21 174.55(17) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.071



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2263051'
loop_
_audit_author_name
_audit_author_address
'juanjuan wang'
;Northwest University
China
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        375
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N2 O3'
_chemical_formula_sum            'C15 H12 N2 O3'
_chemical_formula_weight         268.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7369(6)
_cell_length_b                   9.7927(9)
_cell_length_c                   16.8291(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.727(4)
_cell_angle_gamma                90
_cell_volume                     1252.78(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    16902
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      53.90

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.535
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5060
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16086
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.955
_diffrn_reflns_theta_max         53.898
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2215
_reflns_number_gt                1513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1560P)²+2.7449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2215
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0935
_refine_ls_wR_factor_ref         0.3017
_refine_ls_wR_factor_gt          0.2433
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9138(4) 0.7542(4) 0.3848(2) 0.0504(11) Uani 1 1 d . . . . .
O2 O 0.8196(4) 0.5003(4) 0.2958(2) 0.0459(10) Uani 1 1 d . . . . .
O3 O 0.8923(4) 0.3411(3) 0.39259(19) 0.0387(10) Uani 1 1 d . . . . .
N2 N 0.7568(4) 0.4918(4) 0.4937(2) 0.0325(10) Uani 1 1 d . . . . .
C5 C 0.6968(3) 0.5520(3) 0.55985(13) 0.0324(11) Uani 1 1 d G . . . .
C4 C 0.6002(3) 0.6718(3) 0.55943(13) 0.0323(11) Uani 1 1 d G . . . .
C3 C 0.5456(3) 0.7149(3) 0.62948(16) 0.0377(12) Uani 1 1 d G . . . .
H3 H 0.481025 0.795096 0.629194 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5876(4) 0.6383(3) 0.69995(13) 0.0414(13) Uani 1 1 d G . . . .
H2 H 0.551023 0.667158 0.746819 0.050 Uiso 1 1 calc R U . . .
C1 C 0.6841(4) 0.5185(3) 0.70038(13) 0.0426(13) Uani 1 1 d G . . . .
H1 H 0.712163 0.467222 0.747527 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7387(4) 0.4754(3) 0.63033(16) 0.0380(12) Uani 1 1 d G . . . .
H6 H 0.803306 0.395222 0.630610 0.046 Uiso 1 1 calc R U . . .
C9 C 0.5530(4) 0.8817(4) 0.3799(2) 0.0420(13) Uani 1 1 d G . . . .
H9 H 0.590360 0.923221 0.336339 0.050 Uiso 1 1 calc R U . . .
N1 N 0.5436(3) 0.7475(3) 0.48709(17) 0.0330(10) Uani 1 1 d G . . . .
C7 C 0.3908(4) 0.8250(4) 0.47241(19) 0.0409(13) Uani 1 1 d G . . . .
H7 H 0.300360 0.821847 0.501827 0.049 Uiso 1 1 calc R U . . .
C8 C 0.3967(4) 0.9079(4) 0.4062(2) 0.0435(13) Uani 1 1 d G . . . .
H8 H 0.310936 0.970198 0.383413 0.052 Uiso 1 1 calc R U . . .
C10 C 0.6439(4) 0.7825(3) 0.42990(18) 0.0346(12) Uani 1 1 d G . . . .
C11 C 0.7966(6) 0.7046(5) 0.4155(3) 0.0378(12) Uani 1 1 d . . . . .
C12 C 0.7940(5) 0.5533(5) 0.4324(3) 0.0329(11) Uani 1 1 d . . . . .
C13 C 0.8391(5) 0.4647(5) 0.3653(3) 0.0359(12) Uani 1 1 d . . . . .
C14 C 0.9218(7) 0.2409(6) 0.3326(3) 0.0452(13) Uani 1 1 d . . . . .
H14A H 1.019245 0.268745 0.307438 0.054 Uiso 1 1 calc R U . . .
H14B H 0.817557 0.231858 0.290819 0.054 Uiso 1 1 calc R U . . .
C15 C 0.9626(7) 0.1086(6) 0.3760(3) 0.0517(15) Uani 1 1 d . . . . .
H15A H 0.981634 0.039280 0.338254 0.078 Uiso 1 1 calc R U . . .
H15B H 0.865666 0.082688 0.401100 0.078 Uiso 1 1 calc R U . . .
H15C H 1.066600 0.118626 0.416747 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.225(6) . ?
O2 C13 1.203(5) . ?
O3 C13 1.333(6) . ?
O3 C14 1.456(6) . ?
N2 C12 1.273(6) . ?
N2 C5 1.413(4) . ?
C5 C4 1.3900 . ?
C5 C6 1.3900 . ?
C4 C3 1.3900 . ?
C4 N1 1.423(3) . ?
C3 C2 1.3900 . ?
C3 H3 0.9300 . ?
C2 C1 1.3900 . ?
C2 H2 0.9300 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C9 C8 1.387(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9300 . ?
N1 C10 1.387(2) . ?
N1 C7 1.388(2) . ?
C7 C8 1.386(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.464(6) . ?
C11 C12 1.509(7) . ?
C12 C13 1.516(7) . ?
C14 C15 1.492(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O3 C14 116.8(4) . . ?
C12 N2 C5 126.7(4) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 N2 127.1(2) . . ?
C6 C5 N2 112.8(2) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 N1 121.6(2) . . ?
C3 C4 N1 118.3(2) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C9 C10 108.0 . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
C10 N1 C7 108.0 . . ?
C10 N1 C4 126.8(2) . . ?
C7 N1 C4 123.6(2) . . ?
C8 C7 N1 108.0 . . ?
C8 C7 H7 126.0 . . ?
N1 C7 H7 126.0 . . ?
C7 C8 C9 108.0 . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
N1 C10 C9 108.0 . . ?
N1 C10 C11 123.9(3) . . ?
C9 C10 C11 126.7(3) . . ?
O1 C11 C10 123.1(5) . . ?
O1 C11 C12 120.4(4) . . ?
C10 C11 C12 116.2(4) . . ?
N2 C12 C11 129.1(4) . . ?
N2 C12 C13 116.8(4) . . ?
C11 C12 C13 114.1(4) . . ?
O2 C13 O3 125.0(5) . . ?
O2 C13 C12 123.7(5) . . ?
O3 C13 C12 111.3(4) . . ?
O3 C14 C15 106.9(4) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 C5 C4 28.4(5) . . . . ?
C12 N2 C5 C6 -153.8(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
N2 C5 C4 C3 177.7(3) . . . . ?
C6 C5 C4 N1 -175.2(3) . . . . ?
N2 C5 C4 N1 2.4(3) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
N1 C4 C3 C2 175.4(3) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
N2 C5 C6 C1 -178.0(3) . . . . ?
C5 C4 N1 C10 -46.3(4) . . . . ?
C3 C4 N1 C10 138.4(2) . . . . ?
C5 C4 N1 C7 149.6(2) . . . . ?
C3 C4 N1 C7 -25.8(3) . . . . ?
C10 N1 C7 C8 0.0 . . . . ?
C4 N1 C7 C8 166.7(3) . . . . ?
N1 C7 C8 C9 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C7 N1 C10 C9 0.0 . . . . ?
C4 N1 C10 C9 -166.2(3) . . . . ?
C7 N1 C10 C11 -167.4(4) . . . . ?
C4 N1 C10 C11 26.4(4) . . . . ?
C8 C9 C10 N1 0.0 . . . . ?
C8 C9 C10 C11 167.0(4) . . . . ?
N1 C10 C11 O1 -157.0(4) . . . . ?
C9 C10 C11 O1 38.0(6) . . . . ?
N1 C10 C11 C12 29.4(5) . . . . ?
C9 C10 C11 C12 -135.6(3) . . . . ?
C5 N2 C12 C11 4.4(6) . . . . ?
C5 N2 C12 C13 -174.2(3) . . . . ?
O1 C11 C12 N2 139.3(5) . . . . ?
C10 C11 C12 N2 -46.9(6) . . . . ?
O1 C11 C12 C13 -42.0(6) . . . . ?
C10 C11 C12 C13 131.8(4) . . . . ?
C14 O3 C13 O2 -2.6(6) . . . . ?
C14 O3 C13 C12 173.6(4) . . . . ?
N2 C12 C13 O2 154.2(4) . . . . ?
C11 C12 C13 O2 -24.6(6) . . . . ?
N2 C12 C13 O3 -22.1(5) . . . . ?
C11 C12 C13 O3 159.1(3) . . . . ?
C13 O3 C14 C15 -174.5(4) . . . . ?

_refine_diff_density_max         1.125
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.104



